Sodium cyanoborohydride → 4-Bromo-1-[(2-methoxy-5-methylphenyl)sulfonyl]indoline

HRID 1159759Notes

Reaction equation

HRID 1159759 reaction equation
[BH3-]C#N.[Na+].[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[S:15]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[O:25][CH3:26])(=[O:17])=[O:16]>>[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH2:9][N:10]2[S:15]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[O:25][CH3:26])(=[O:16])=[O:17]

Participants

3

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 687168404-Bromo-1-[(2-methoxy-5-methylphenyl)sulfonyl]-1H-indole2×

Product 1

HCID 687178864-Bromo-1-[(2-methoxy-5-methylphenyl)sulfonyl]indolineYield 80.8%

Procedure

NaBH3CN (480 mg, 7.63 mmol) was added portionwise, under N2, to ice cold TFA (15 mL). The mixture was stirred for 15 min. and 4-bromo-1-[(2-methoxy-5-methylphenyl)sulfonyl]-1H-indole (645 mg, 1.70 mmol; Intermediate 6) was added in portions. The mixture was allowed to attain rt. and stirred 1.5 h. Additional NaBH3CN (480 mg, 7.63 mmol) was added with continuous stirring 1 h. The reaction mixture was quenched with water (30 mL) and extracted twice with DCM. The DCM layers were combined and extracted with aq. Na2CO3 (˜pH 10). The organic layer was dried, filtered and concentrated to give the title compound (525 mg, 80%) as a yellow viscous oil. MS (ESI+) for C16H16BrNO3S m/z 382 (M+H)+.

Workup

  1. customto attain rt
  2. stirringand stirred 1.5 h
  3. stirringwith continuous stirring 1 h
  4. customThe reaction mixture was quenched with water (30 mL)
  5. extractionextracted twice with DCM
  6. extractionextracted with aq. Na2CO3 (˜pH 10)
  7. customThe organic layer was dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-105d4c844cba44ffa6d42298931b3b80
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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