Water → 2-(1-(3-cyano-4-fluorophenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

HRID 1754463Notes

Reaction equation

HRID 1754463 reaction equation
B(Br)(Br)Br.C[O:6][C:7](=[O:31])[CH2:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]#[N:29])[CH:22]=2)(=[O:20])=[O:19])[C:10]=1[CH3:30].O>C(Cl)Cl>[C:28]([C:23]1[CH:22]=[C:21]([S:18]([N:11]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:17]3[C:9]([CH2:8][C:7]([OH:31])=[O:6])=[C:10]2[CH3:30])(=[O:19])=[O:20])[CH:26]=[CH:25][C:24]=1[F:27])#[N:29]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67219319[1-(3-cyano-4-fluoro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Product 1

HCID 114944962-(1-(3-cyano-4-fluorophenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1M BBr3 in CH2Cl2 (7.66 mL, 7.66 mmol) is added to a solution of [1-(3-cyano-4-fluoro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (0.495 g, 1.27 mmol) in CH2Cl2 (2 mL). The reaction mixture is exposed to microwave irradiation at 60° C. for 45 minutes. Water is added to the reaction mixture which is stirred for further 20 minutes. The organic layer is isolated using the Isolute™ phase separator cartridge and evaporated. The residue is loaded on a pre-packed Isolute™ silica column and eluted using a gradient eluent from 100% CH2Cl2 to 5% methanol in CH2Cl2 to afford the title compound; MH+=374.

Workup

  1. customirradiation at 60° C. for 45 minutes
  2. customThe organic layer is isolated
  3. customevaporated
  4. washeluted

Sources & evidence

ORD record
ord-7c6ff16633694d4da7c47fe7ca3ed177
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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