Water → HCID 68239709, compound

HRID 1776835Notes

Reaction equation

HRID 1776835 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]([C:18]2[C:19]([N:38]([CH3:43])[S:39]([CH3:42])(=[O:41])=[O:40])=[CH:20][C:21]3[O:25][C:24]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[C:23]([C:33]([NH:35][CH3:36])=[O:34])[C:22]=3[CH:37]=2)[CH:13]=[CH:14][C:15]=1[O:16]C.B(Br)(Br)Br.O>ClCCl>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:24]2[O:25][C:21]3[CH:20]=[C:19]([N:38]([CH3:43])[S:39]([CH3:42])(=[O:40])=[O:41])[C:18]([C:12]4[CH:13]=[CH:14][C:15]([OH:16])=[C:10]([C:2]5[NH:1][C:9]6[C:4]([CH:3]=5)=[CH:5][CH:6]=[CH:7][CH:8]=6)[CH:11]=4)=[CH:37][C:22]=3[C:23]=2[C:33]([NH:35][CH3:36])=[O:34])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 68239677HCID 68239677, compound

Product 1

HCID 68239709HCID 68239709, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3-(1H-indol-2-yl)-4-methoxyphenyl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 g, 0.16 mmol) in dichloromethane (2 mL) was added dropwise BBr3 (0.2 mL) at 0° C., Then warmed up to room temperature and stirred for 5 hours. Water was added, extracted with dichloromethane and washed with brine, dried over Na2SO4. After concentrated, the resulting residue was purified using Prep-TLC to provide the product of 2-(4-fluorophenyl)-5-(4-hydroxy-3-(1H-indol-2-yl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (30 mg, yield: 31%). 1H-NMR (CDCl3, 400 MHz) δ 9.30 (s, 1H), 8.75 (s, 1H), 7.79˜8.30 (m, 2H), 7.54 (d, J=7.6 Hz, 1H), 7.50 (s, 1H), 7.37 (d, J=1.6 Hz, 1H), 6.91˜7.19 (m, 7H), 6.65 (d, J=1.2 Hz, 1H), 6.01 (d, J=4.4 Hz, 1H), 2.95 (d, J=4.8 Hz, 3H), 2.61 (s, 3H), 2.43 (s, 3H). MS (M+H)+: 584.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-515eff9f7b244fd49d2ad6e3243808f9
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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