Sodium borohydride → 6-(1-Hydroxy-indan-5-yloxy)-nicotinamide

HRID 422209Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[BH4-].[Na+]>>[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 597506396-(1-Oxo-indan-5-yloxy)-nicotinamide2×

Product 1

HCID 666734706-(1-Hydroxy-indan-5-yloxy)-nicotinamideYield 68.8%

Procedure

Using a method similar to intermediate 13, using 6-(1-Oxo-indan-5-yloxy)-nicotinamide (Intermediate 4, 500 mg, 1.86 mmol) and NaBH4 (105 mg, 2.79 mmol) gives 6-(1-Hydroxy-indan-5-yloxy)-nicotinamide (346 mg) as a white solid. Mass spectrum (ion spray): m/z=271 (M+1); 1HNMR (DMSO-d6): 8.58 (s, 1H), 8.22 (d, 1H), 8.00 (s, 1H), 7.45 (s, 1H), 7.34 (d, 1H), 7.03 (d, 1H), 6.97 (s, 1H), 6.93 (d, 1H), 5.03 (t, 1H), 2.93-2.86 (m, 1H), 2.73-2.66 (m, 1H), 2.38-2.30 (m, 1H), 1.84-1.72 (m, 1H), 1.33 (s, 1H). Convert 6-(1-Hydroxy-indan-5-yloxy)-nicotinamide to the title compound using a method similar to intermediate 13. Due to instability, use this material without purification.

Sources & evidence

ORD record: ord-18d4056e41eb4f4db22e0ffc5d16ad9d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101638B2

Reaction notes

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