Ammonium formate → 2-(4-Aminophenyl)-6-hydroxy-3-[3-methoxy-4-(1-pyrrolidinyl)-benzyl]benzo[b]thiophene

HRID 1595927Notes

Reaction equation

HRID 1595927 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17]CC4C=CC=CC=4)[CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:25][C:26]2[CH:31]=[CH:30][C:29](CN3CCCC3)=[C:28]([O:38][CH3:39])[CH:27]=2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+:43]>C1COCC1.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:10]=3[C:9]=2[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N:43]3[CH2:4][CH2:3][CH2:2][CH2:7]3)=[C:28]([O:38][CH3:39])[CH:27]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 155495242-(4-Aminophenyl)-6-benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophene

Product 1

HCID 224627022-(4-Aminophenyl)-6-hydroxy-3-[3-methoxy-4-(1-pyrrolidinyl)-benzyl]benzo[b]thiophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Aminophenyl)-6-benzyloxy 3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophene (103 mg) in THF (4.0 mL) was treated with a solution of ammonium formate (25% in H2O, 2.0 mL) and 10% palladium on carbon (100 mg) sequentially at ambient temperature. The resulting mixture was stirred at ambient temperature under argon for 21 h before filtered through diatomaceous earth followed by rinsing with dichloromethane and methanol. The filtrate was extracted with dichloromethane (20 mL×3) from water (30 mL). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:10:85) afforded the product (80 mg).

Workup

  1. filtrationbefore filtered through diatomaceous earth
  2. washby rinsing with dichloromethane and methanol
  3. extractionThe filtrate was extracted with dichloromethane (20 mL×3) from water (30 mL)
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07024d15ac8749e8add29a949e81de57
Source dataset
uspto-grants-2001_09
Patent number
US06288105B1

Reaction notes

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