1-(2-Fluorophenyl)piperazine → 1-(3-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-3-yl)propyl)-4-(2-fluorophenyl)piperazine

HRID 387070Notes

Reaction equation

[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH:19]=O)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH2:19][N:31]2[CH2:30][CH2:29][N:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[F:21])[CH2:33][CH2:32]2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 705291-(2-Fluorophenyl)piperazine

HCID 81531Diisopropylethylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 866399233-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-3-yl)propanal

Product 1

HCID 250639881-(3-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-3-yl)propyl)-4-(2-fluorophenyl)piperazine

Procedure

142 mg (82%) of target compound was obtained by using a method same as in Example 1 by using 3-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-3-yl)propanal (100 mg, 0.365 mmol), 1-(2-fluorophenyl)piperazine (66 mg, 0.365 mmol), DIPEA (0.1 mL, 0.548 mmol) and NaBH(OAc)3 (232 mg, 1.095 mmol).

Workup

custom142 mg (82%) of target compound was obtained

Sources & evidence

ORD record: ord-063d543cfb69480ba25187e9604eeafd
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372844B2

Reaction notes

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