Sodium borohydride → HCID 54720166, compound

HRID 1244095Notes

Reaction equation

HRID 1244095 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([OH:24])=[C:21]([C:25]#[N:26])[C:20](=[O:27])[NH:19][C:18]=3[S:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:2].[BH4-].[Na+]>CO.ClCCl>[OH:24][C:22]1[C:23]2[C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[CH2:1][OH:2])=[CH:14][CH:13]=3)=[CH:16][S:17][C:18]=2[NH:19][C:20](=[O:27])[C:21]=1[C:25]#[N:26]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 546899423-(2'-Formyl-1,1'-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 54720166HCID 54720166, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2′-formyl-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.03 g, 0.08 mmol) in MeOH (2 mL) and dichloromethane (0.5 mL) was added NaBH4 (0.012 g, 0.32 mmol) in a single portion. The reaction was stirred at room temperature for 18 h. It was then cooled to 0° C. in an ice bath, quenched by slow addition of 1N HCl (10 mL) and extracted with dichloromethane (3×10 mL). The organic layers were dried with anhydrous sodium sulfate, concentrated and purified by RP-HPLC to give the title compound as a white solid. MS (ESI) m/e 372.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 12.42 (br s, 1H), 7.60 (dd, 1H), 7.50 (d, 2H), 7.32–7.42 (m, 4H), 7.26 (dd, 1H), 7.07 (s, 1H), 4.46 (s, 2H).

Workup

  1. temperatureIt was then cooled to 0° C. in an ice bath
  2. customquenched by slow addition of 1N HCl (10 mL)
  3. extractionextracted with dichloromethane (3×10 mL)
  4. dry with materialThe organic layers were dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-49d6c93806014e2aabd2c7ca55065351
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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