Phenylpropanolamine → (1R,2S)-1-[1-(4-fluorophenyl)indazol-4-yl]oxy-1-phenyl-propan-2-amine

HRID 1661448Notes

Reaction equation

HRID 1661448 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](O[C@H](C4C=CC=CC=4)[C@@H](N)C)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.IC1C=CC=C2C=1C=NN2C1C=CC(F)=CC=1.[CH3:45][C@H:46]([NH2:55])[C@H:47]([OH:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[C:12]([O:54][C@H:47]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C@@H:46]([NH2:55])[CH3:45])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10297PhenylpropanolamineHCID 59339817(alphaS,betaR)-beta-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-alpha-methylbenzeneethanamineHCID 666878174-Iodo-1-(4-fluorophenyl)indazole

Product 1

HCID 66687159(1R,2S)-1-[1-(4-fluorophenyl)indazol-4-yl]oxy-1-phenyl-propan-2-amine

Procedure

Prepared according to the protocol described for 1a starting from 4-iodo-1-(4-fluorophenyl)indazole (3b, 332 mg, 0.98 mmol) and (1R,2S)-norephedrine (742 mg, 4.9 mmol). Yield: 150 mg (42%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b76251966238409cbed65a353b4c6ddd
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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