Sodium borohydride → HCID 22676727, compound

HRID 1006258Notes

Reaction equation

HRID 1006258 reaction equation
[BH4-].[Na+].[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[C:10]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH:25]=[O:26])[CH:21]=4)[N:16]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=4)[C:15]=3[C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:11]=[CH:12][CH:13]=2)[CH2:5][CH2:4]1>CO>[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[C:10]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][OH:26])[CH:21]=4)[N:16]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=4)[C:15]=3[C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:11]=[CH:12][CH:13]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22676773HCID 22676773, compound

Product 1

HCID 22676727HCID 22676727, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (38 mg, 1.0 mmol) was added to a stirred solution of ethyl 3-[3-(cyclopropylmethoxy)phenyl]-1-(3-methoxybenzyl)-5-(2-oxoethoxy)-1H-indole-2-carboxylate (Example 136, 380 mg, 0.74 mmol) in methanol (10 mL). The reaction was stirred for 2 h and then the reaction was quenched with water (100 mL). The product was extracted with ethyl acetate (3×40 mL) and then the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to leave 363 mg (95%) of product containing some impurities. The material was used in the next reaction without further purification. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.34-7.46 (m, 3 H), 7.16 (dd, 1 H), 6.93-7.02 (m, 4 H), 6.65-6.81 (m, 3 H), 5.78 (s, 2 H), 3.82-4.23 (m, 9 H), 3.69 (s, 3 H), 1.24-1.34 (m, 1 H), 1.02 (t, 3 H), 0.60-0.70 (m, 2 H), 0.34-0.44 (m, 2 H).

Workup

  1. customthe reaction was quenched with water (100 mL)
  2. extractionThe product was extracted with ethyl acetate (3×40 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3622f90988754df8b23fa67e394c4466
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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