Diisobutylaluminum hydride → HCID 58415340, compound

HRID 2075174Notes

Reaction equation

[CH2:1]([C:8]1[CH:16]=[CH:15][C:14]2[C:10](=[CH:11][N:12]([C:17]3[CH:27]=[CH:26][C:20]([C:21](OCC)=[O:22])=[CH:19][C:18]=3[F:28])[N:13]=2)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC2C(=CN(C3C=CC(C(OCC4C=CC=CC=4)=O)=CC=3F)N=2)C=1)C1C=CC=CC=1.CC(C[AlH]CC(C)C)C>ClCCl>[CH2:1]([C:8]1[CH:16]=[CH:15][C:14]2[C:10](=[CH:11][N:12]([C:17]3[CH:27]=[CH:26][C:20]([CH2:21][OH:22])=[CH:19][C:18]=3[F:28])[N:13]=2)[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a mixture (171 mg) of ethyl 4-(5-benzyl-2H-indazol-2-yl)-3-fluorobenzoate and benzyl 4-(5-benzyl-2H-indazol-2-yl)-3-fluorobenzoate in dichloromethane (10 mL) was added 1.0 M solution of DIBAL-H (1.37 mL, 1.37 mmol) in dichloromethane slowly at −78° C. The mixture stirred for 1 hour at −78° C. followed by quenching at −78° C. with 0.5 mL of a saturated solution of ammonium chloride. Hydrochloric acid (2N, 0.6 mL) was added, the cooling bath removed, and the mixture stirred for 1 hour. The mixture was subsequently extracted with dichloromethane and the extracts were dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give (4-(5-benzyl-2H-indazol-2-yl)-3-fluorophenyl)methanol. MS (ESI) m/z: Calculated: 332.37; Observed: 333.3 (M++1).

Workup

customby quenching at −78° C. with 0.5 mL of a saturated solution of ammonium chloride
additionHydrochloric acid (2N, 0.6 mL) was added
customthe cooling bath removed
stirringthe mixture stirred for 1 hour
extractionThe mixture was subsequently extracted with dichloromethane
dry with materialthe extracts were dried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-a4fdcd86c20140dbb163d3ca220a014e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919519B2

Reaction notes

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