Tetrahydrofuran → 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)propan-1-ol
Reaction equation
C[O:2][C:3](=O)[CH:4]([N:6]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:8]([I:15])=[CH:7]1)[CH3:5].[BH4-].[Li+].C1COCC1>CCO>[I:15][C:8]1[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[N:6]([CH:4]([CH3:5])[CH2:3][OH:2])[CH:7]=1Participants
Procedure
To a solution of 2-(3-iodo-pyrrolo[3,2-c]pyridine-1-yl)-propionic acid methyl ester (Preparation 57, 18.1 g, 54.8 mmol) in EtOH (300 mL) was added 2M lithium borohydride solution in THF (63.1 mL, 126 mol) at 0° C. The reaction was stirred at this temperature for 30 minutes before warming to room temperature for 18 hours. The reaction was quenched by the addition of water (300 mL) at 0° C. with stirring for 1 hour. The EtOH was removed in vacuo and the resulting residue diluted further with water (600 mL) followed by extraction into 5% MeOH in DCM (250 mL). The organic layer was collected, dried over MgSO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-5% MeOH in DCM to afford the title compound (12 g, 73%).
Workup
- customThe reaction was quenched by the addition of water (300 mL) at 0° C.
- stirringwith stirring for 1 hour
- customThe EtOH was removed in vacuo
- additionthe resulting residue diluted further with water (600 mL)
- extractionfollowed by extraction into 5% MeOH in DCM (250 mL)
- customThe organic layer was collected
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified
- washeluting with 0-5% MeOH in DCM
Sources & evidence
- ORD record
- ord-01b5a0bbfa2c4b0f87e3254130b4ceb4
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163021B2
Reaction notes
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