Sodium borohydride → HCID 67079366, compound

HRID 453395Notes

Reaction equation

HRID 453395 reaction equation
CO[C:3](=[O:28])[C:4]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:16]=2[F:25])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[C:26]#[N:27].[BH4-].[Na+]>CO.C(Cl)Cl.O.O.O.O.O.O.[Co](Cl)Cl>[CH3:11][O:10][C:8]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:13][C:12]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:16]=1[F:25])[C:3](=[O:28])[NH:27][CH2:26]2)=[O:9]

Participants

6

Reactant 2

HCID 4311764Sodium borohydride2×HCID 67079577HCID 67079577, compound

Product 1

HCID 67079366HCID 67079366, compoundYield 49.4%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-cyano-5-(2-fluoro-4-trimethylsilanylphenylamino)-terephthalic acid dimethyl ester (300 mg, 0.75 mmol) in methanol (15 ml) and DCM (2 ml) at 0° C. was added silica (1 g) and cobalt (II) chloride hexahydrate (357 mg, 1.50 mmol) followed by sodium borohydride (285 mg, 7.50 mmol). During the addition of the sodium borohydride large amounts of effervescence were observed and the reaction turned black. The reaction mixture was stirred at 0° C. for 1 hour. The reaction was filtered and the filtrate concentrated in vacuo to provide a residu that was subjected to flash chromatography (SiO2, gradient 0-20% methanol in DCM) to yield the title compound as a brown solid (138 mg, 49%). LCMS (Method B): RT=4.18 min, 2M+H−=745 (100%), M+H+=373 (25%).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto provide a residu that

Sources & evidence

ORD record
ord-a600145ade644bf8b5e28d26ae7cc092
Source dataset
uspto-grants-2013_07
Patent number
US08492427B2

Reaction notes

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