Sodium borohydride → N-(2,4-difluorophenyl)-8-(hydroxymethyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

HRID 628116Notes

Reaction equation

HRID 628116 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:27])[C:10]([C:12]1[S:24][C:23]2[C:22]3[CH:21]=[C:20]([CH:25]=[O:26])[CH:19]=[CH:18][C:17]=3[O:16][CH2:15][C:14]=2[CH:13]=1)=[O:11].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:27])[C:10]([C:12]1[S:24][C:23]2[C:22]3[CH:21]=[C:20]([CH2:25][OH:26])[CH:19]=[CH:18][C:17]=3[O:16][CH2:15][C:14]=2[CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57900416N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

Product 1

HCID 57900161N-(2,4-difluorophenyl)-8-(hydroxymethyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cooled solution of N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide in ethanol (1 mL) was added sodium borohydride (10 mg, 0.3 mmol, 6 equiv). After 3 hr, excess sodium borohydride was quenched with saturated aqueous ammonium chloride solution (3 mL). The ethanol was removed in vacuo, and the resulting aqueous solution was extracted with ethylacetate (3×3 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (3:2 hexanes/ethylacetate) provided 159bp (5.2 mg, 30%). 1H NMR (500 MHz, CDCl3) δ 7.26 (m, 1H), 7.15 (m, 1H), 7.05 (m, 1H), 6.86-6.93 (m, 4H), 5.25 (s, 2H), 4.55 (d, J=6.7 Hz, 2H), 4.06 (m, 1H), 3.40 (s, 3H). LCMS (ESI) m/z: 388.1.

Workup

  1. customexcess sodium borohydride was quenched with saturated aqueous ammonium chloride solution (3 mL)
  2. customThe ethanol was removed in vacuo
  3. extractionthe resulting aqueous solution was extracted with ethylacetate (3×3 mL)
  4. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (3:2 hexanes/ethylacetate)
  8. customprovided 159bp (5.2 mg, 30%)

Sources & evidence

ORD record
ord-3bb1b5c515fe42aa98d5a9552dcb94f7
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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