Potassium Carbonate → tert-butyl 2-(6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-(2-hydroxyethyl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate

HRID 595750Notes

Reaction equation

HRID 595750 reaction equation
C([O:3]/[CH:4]=[CH:5]/[C:6]1[C:7]([C:38]2[N:39]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[C:40]3[C:45]([C:46]=2[CH3:47])=[CH:44][CH:43]=[CH:42][CH:41]=3)=[N:8][C:9]([C:12]2[C:13]([N:32]([CH3:37])[S:33]([CH3:36])(=[O:35])=[O:34])=[CH:14][C:15]3[O:19][C:18]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)=[C:17]([C:27](=[O:30])[NH:28][CH3:29])[C:16]=3[CH:31]=2)=[CH:10][CH:11]=1)C.[BH4-].[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.CCOC(C)=O>[F:26][C:23]1[CH:22]=[CH:21][C:20]([C:18]2[O:19][C:15]3[CH:14]=[C:13]([N:32]([CH3:37])[S:33]([CH3:36])(=[O:34])=[O:35])[C:12]([C:9]4[N:8]=[C:7]([C:38]5[N:39]([C:48]([O:50][C:51]([CH3:54])([CH3:52])[CH3:53])=[O:49])[C:40]6[C:45]([C:46]=5[CH3:47])=[CH:44][CH:43]=[CH:42][CH:41]=6)[C:6]([CH2:5][CH2:4][OH:3])=[CH:11][CH:10]=4)=[CH:31][C:16]=3[C:17]=2[C:27](=[O:30])[NH:28][CH3:29])=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 90333599(E)-tert-butyl 2-(3-(2-ethoxyvinyl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate

Product 1

HCID 90333639tert-butyl 2-(6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-(2-hydroxyethyl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-tert-butyl 2-(3-(2-ethoxyvinyl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate (72 mg, 0.096 mmol) in THF (0.350 mL) at 0° C. was added Mercuric acetate (36.6 mg, 0.115 mmol) in H2O (0.350 mL). After stirring the resultant mixture at 0° C. for 30 min, NaBH4 (14.47 mg, 0.383 mmol) in 0.580 mL of saturated (aq) K2CO3 solution was added and the reaction mixture was warmed to ambient temperature. After 1.5 h at ambient temperature, the reaction mixture was diluted with EtOAc and washed successively with H2O (2×) and brine (1×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 0-90% EtOAc/CH2Cl2 as eluent. 1H NMR δ (ppm) (CHCl3-d): 8.16 (1H, d, J=8.33 Hz), 8.03˜7.99 (3H, m), 7.87 (1H, d, J=7.99 Hz), 7.69˜7.65 (2H, m), 7.57 (1H, d, J=7.77 Hz), 7.39 (1H, t, J=7.73 Hz), 7.33 (1H, t, J=7.42 Hz), 7.22 (2H, t, J=8.58 Hz), 5.95 (1H, br s), 3.81 (2H, m), 3.19 (3H, s), 3.00 (3H, d, J=4.88 Hz), 2.98˜2.83 (2H, m), 2.78 (3H, s), 2.11 (3H, s), 1.45 (6H, s), 1.27 (3H, s). MS (M+H): 727.

Workup

  1. washwashed successively with H2O (2×) and brine (1×)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2932fb943cea4f50b44aea0a6216012d
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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