Sodium borohydride → 3'-Fluoro-4'-[3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N-methylbiphenyl-2-sulfonamide

HRID 1523960Notes

Reaction equation

HRID 1523960 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:21]2[C:22]([S:27]([NH:30][CH3:31])(=[O:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[C:12]2[C:18]([CH:19]=[O:20])=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1>CO>[F:3][C:4]1[CH:5]=[C:6]([C:21]2[C:22]([S:27]([NH:30][CH3:31])(=[O:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[C:12]2[C:18]([CH2:19][OH:20])=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 903128853'-fluoro-4'-(3-formyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-N-methyl-[1,1'-biphenyl]-2-sulfonamide

Product 1

HCID 903149583'-Fluoro-4'-[3-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N-methylbiphenyl-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (4.45 mg, 0.13 mmol) was added to 3′-fluoro-4′-(3-formyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-N-methyl-[1,1′-biphenyl]-2-sulfonamide (18 mg, 0.044 mmol) in MeOH (0.52 mL). The mixture was stirred at rt for 1 h and then concentrated to dryness. The residue was subjected to FCC purification to give the title compound. MS (ESI): mass calcd. for C21H18FN3O3S, 411.11; m/z found, 412.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 9.36 (s, 1H), 8.34 (s, 1H), 8.23 (dd, J=7.9, 1.2, 1H), 8.12 (s, 1H), 7.68-7.61 (m, 1H), 7.61-7.54 (m, 1H), 7.42-7.30 (m, 5H), 5.21 (s, 1H), 4.88 (s, 2H), 2.52 (dd, J=13.9, 5.3, 3H).

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was subjected to FCC purification

Sources & evidence

ORD record
ord-3054b21a3c854676ab52ca8a8a766a23
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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