Dichloromethane → 3-(3-Hydroxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one hydrochloride

HRID 920929Notes

Reaction equation

HRID 920929 reaction equation
C[O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[C:13]2[C:14](=[O:30])[N:15]([CH2:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH:16]=[CH:17][C:12]=2[S:11][CH:10]=1.B(Br)(Br)Br.[OH-].[Na+].C(Cl)[Cl:38]>>[ClH:38].[OH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[C:13]2[C:14](=[O:30])[N:15]([CH2:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH:16]=[CH:17][C:12]=2[S:11][CH:10]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 866831393-(3-Methoxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one

Product 1

HCID 866831413-(3-Hydroxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one hydrochloride

Procedure

To 3-(3-methoxypyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[3,2-c]pyridin-4(5H)-one (50.0 mg, 0.121 mmol) in DCM (20 mL) was added 1M BBr3 in DCM (0.363 mmol, 91 mg). The reaction mixture was stirred for 2 h under nitrogen. The reaction mixture was poured onto water and basified with 1N NaOH, extracted with DCM and dried. The organic phase was concentrated to dryness and the residue was purified by column chromatography (normal phase) on silica using DCM/methanol to give the title compound (13 mg, 0.030 mmol).

Workup

  1. extractionextracted with DCM
  2. customdried
  3. concentrationThe organic phase was concentrated to dryness
  4. customthe residue was purified by column chromatography (normal phase) on silica

Sources & evidence

ORD record
ord-054df993ac064b89bde66a4aad5b29e2
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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