Sodium borohydride → HCID 67449271, compound

HRID 1853879Notes

Reaction equation

HRID 1853879 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]3[C:12]4[CH:24]=[CH:23][S:22][C:13]=4[C:14](=[O:21])[NH:15][C:16]=3[CH:17]=[CH:18][C:19]=2[OH:20])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(O)C>[OH:20][C:19]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:21])[C:13]3[S:22][CH:23]=[CH:24][C:12]=3[C:11]=2[C:10]=1[C:7]1[CH:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226445Aluminium lithium hydrideHCID 67447763HCID 67447763, compound

Product 1

HCID 67449271HCID 67449271, compoundYield 1.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9-(4-acetylphenyl)-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (200 mg, 0.59 mmol) in ethanol (4 mL) was cooled to 0° C. and sodium borohydride (45 mg, 1.2 mmol) was added. The reaction mixture was stirred at room temperature for 18 h however starting material was present. The reaction was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 1.2 mL, 1.2 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction was cooled to 0° C., quenched with methanol and concentrated. The residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (2.6 mg, 1%) as a light brown solid: 1H NMR (300 MHz, CD3OD) δ 7.59-7.52 (m, 3H), 7.39 (d, J=8.9 Hz, 1H), 7.29-7.25 (m, 2H), 7.16 (d, J=8.9 Hz, 1H), 6.03 (d, J=5.4 Hz, 1H), 4.97 (q, J=6.4 Hz, 1H), 1.56 (d, J=6.5 Hz, 3H); ESI MS m/z 338 [C19H15NO3S+H]+; HPLC 98.6% (AUC), tR=9.78 min.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringthe reaction mixture was stirred at room temperature for 2 h
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with methanol
  5. concentrationconcentrated
  6. customThe residue was purified by preparatory HPLC (C18 silica, water/acetonitrile

Sources & evidence

ORD record
ord-84c8f05722df4636a551467d5a3c8090
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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