Binap, (A+-)- → HCID 66700940, compound

HRID 1253726Notes

Reaction equation

CC(C)([O-])C.[Na+].[CH2:7]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10][CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].Cl[C:25]1[N:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:32][C:31]([F:34])([F:33])[C:28]1[CH:27]=[N:26][C:25]([N:14]2[CH2:13][CH2:12][C:11]3([CH2:7][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:9][CH2:10]3)[CH2:16][CH2:15]2)=[N:30][CH:29]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium t-butoxide (625 mg, 6.51 mmol, 3.0 eq.) was added to a stirred solution of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (600 mg, 2.17 mmol, 1.0 eq.) and 2-chloro-5-(trifluoromethyl)pyrimidine (391 mg, 2.17 mmol, 1.0 eq.) in toluene (15 ml) and the reaction mixture was degassed with nitrogen. BINAP (80 mg, 0.13 mmol, 0.06 eq.) and Pd(OAc)2 (10 mg, 0.04 mmol, 0.02 eq.) were added and the resulting mixture was heated at 120° C. for 16 h. The reaction mixture was filtered through celite and the filtrate was evaporated under reduced pressure to afford the crude product which was purified by column chromatography (silica gel; 0-1% MeOH/MC) to yield the pure desired product as a white solid. Yield: 41% (350 mg, 1.2 mmol).

Workup

customthe reaction mixture was degassed with nitrogen
filtrationThe reaction mixture was filtered through celite
customthe filtrate was evaporated under reduced pressure
customto afford the crude product which
customwas purified by column chromatography (silica gel; 0-1% MeOH/MC)

Sources & evidence

ORD record: ord-e97c7892c5a24ba6a5a2cc6935585a4d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455475B2

Reaction notes

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