Sodium cyanoborohydride → [3,5-Dichloro-4-(4-chloro-thiazolo[5,4-c]pyridin-2-yl)-phenyl]-methanol

HRID 2366223Notes

Reaction equation

HRID 2366223 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:20])[C:9]=1[C:10]1[S:11][C:12]2[C:13]([Cl:19])=[N:14][CH:15]=[CH:16][C:17]=2[N:18]=1)[CH:5]=[O:6].C([BH3-])#N.[Na+]>C(Cl)Cl.CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([Cl:20])[C:9]=1[C:10]1[S:11][C:12]2[C:13]([Cl:19])=[N:14][CH:15]=[CH:16][C:17]=2[N:18]=1

Participants

6

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 866690003,5-Dichloro-4-(4-chloro-thiazolo[5,4-c]pyridin-2-yl)-benzaldehyde

Product 1

HCID 86668999[3,5-Dichloro-4-(4-chloro-thiazolo[5,4-c]pyridin-2-yl)-phenyl]-methanolYield 100.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3,5-dichloro-4-(4-chloro-thiazolo[5,4-c]pyridin-2-yl)-benzaldehyde (0.065 g, 0.19 mmol) in DCM (0.5 mL), MeOH (0.5 mL) and acetic acid (0.5 mL) was treated with sodium cyanoborohydride (0.013 g, 0.21 mmol) and the resultant mixture was stirred for 2 hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution and partitioned between DCM and water. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the desired compound as an off-white solid (0.066 g, quant. yield). 1H NMR (300 MHz, CDCl3): δ 8.52 (d, J=5.6 Hz, 1H), 7.99 (d, J=5.6 Hz, 1H), 7.49 (s, 2H), 4.79 (s, 2H).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution
  2. custompartitioned between DCM and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-095b45490dfe4442bbc09d3241fa9a1e
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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