Sodium Iodide → HCID 178485252, compound

HRID 595546Notes

Reaction equation

HRID 595546 reaction equation
[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:40]([CH3:45])[S:41]([CH3:44])(=[O:43])=[O:42])=[CH:21][C:22]6[O:26][C:25]([C:27]7[C:28]([O:33]C)=[N:29][CH:30]=[CH:31][CH:32]=7)=[C:24]([C:35]([NH:37][CH3:38])=[O:36])[C:23]=6[CH:39]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.[Na+].[I-]>CC(O)=O>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:40]([CH3:45])[S:41]([CH3:44])(=[O:43])=[O:42])=[CH:21][C:22]6[O:26][C:25]([C:27]7[C:28]([OH:33])=[N:29][CH:30]=[CH:31][CH:32]=7)=[C:24]([C:35]([NH:37][CH3:38])=[O:36])[C:23]=6[CH:39]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 77845411HCID 77845411, compound

Product 1

HCID 178485252HCID 178485252, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(2-methoxypyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (45 mg, 0.07 mmol) and NaI (54 mg, 0.36 mmol) in HOAc (1 mL) was stirred at 100° C. under N2 for 5 h. After the reaction, it was extracted with EtOAc (10 mL×3) and Na2CO3 (a.q., 5 mL). The organic layer was washed with brine (5 mL×3), dried over aq. Na2SO4 and concentrated. The residue was purified by prep-HPLC to give 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(2-hydroxypyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (10 mg, yield: 23%). 1H-NMR (CDCl3, 400 MHz) δ 8.20 (s, 1H), 8.11 (s, 1H), 7.97 (d, J=5.2 Hz, 1H), 7.96 (s, 1H), 7.66 (d, J=1.2 Hz, 1H), 7.55 (m, 2H), 7.23 (s, 2H), 7.14 (d, J=8.4 Hz, 1H), 6.85 (s, 1H), 6.60 (t, J=6.8 Hz, 1H), 6.01 (s, 2H), 5.30 (s, 1H), 3.41 (s, 3H), 2.96 (d, J=4.8 Hz, 3H), 2.70 (s, 3H). MS (M+H)+: 614.

Workup

  1. customAfter the reaction, it
  2. extractionwas extracted with EtOAc (10 mL×3) and Na2CO3 (a.q., 5 mL)
  3. washThe organic layer was washed with brine (5 mL×3)
  4. dry with materialdried over aq. Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-677d781d6b5b4f0398fbb7377ee7c982
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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