Methanol → 1-[(4-Methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine-3-methanol

HRID 41584Notes

Reaction equation

HRID 41584 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH:20]=[O:21])=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CO>>[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([CH2:20][OH:21])=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 454802961-Tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 672518311-[(4-Methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine-3-methanolYield 80%

Procedure

To a stirred solution of 1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde [956716-93-1] (2.0 g, 6.66 mmol) in methanol (20 mL) NaBH4 (0.756 g, 20 mmol) was added in portions at 0° C. Then the mixture was allowed to warm to rt and stirred for 18 h. Methanol was evaporated under reduced pressure and water was added to the stirred residue. The resulting precipitate was filtered off and dried under vacuum to yield the title compound as a white solid (1.6 g, 80%). [1H NMR (400 MHz, CHLOROFORM-d) ♀ ppm 8.45 (dd, J=4.8, 3.2 Hz, 1H), 8.07 (d, J=8.4 Hz, 2H), 7.96 (dd, J=8.0, 1.6 Hz, 1H), 7.70 (s, 1H), 7.26 (d, J=8.4 Hz, 2H), 7.20 (dd, J=7.6, 4.8 Hz, 1H), 4.83 (d, J=5.2 Hz, 2H), 2.37 (s, 3H), 1.73 (t, J=5.2 Hz, 1H); LCMS RtE=0.85, [M+H]+=302.8].

Workup

  1. customMethanol was evaporated under reduced pressure and water
  2. additionwas added to the stirred residue
  3. filtrationThe resulting precipitate was filtered off
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8103343396264bbdb471a78ecd5d6566
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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