Potassium Carbonate → HCID 24985020, compound

HRID 388126Notes

Reaction equation

[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:26][CH3:27])=[C:8]([C:10]2[N:15]=[C:14]([NH:16][C@@H:17]([CH:20]([CH3:22])[CH3:21])[CH2:18][OH:19])[C:13]([N+:23]([O-])=O)=[CH:12][CH:11]=2)[CH:9]=1)([CH3:3])[CH3:2].ClC1N=C(N[C@@H](C(C)C)[CH2:37][OH:38])C([N+]([O-])=O)=CC=1.C(C1C=CC(OC)=C(B(O)O)C=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:19][CH2:18][C@@H:17]([N:16]1[C:14]2=[N:15][C:10]([C:8]3[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=[CH:6][C:7]=3[O:26][CH3:27])=[CH:11][CH:12]=[C:13]2[NH:23][C:37]1=[O:38])[CH:20]([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 85 °C

Procedure

(S)-2-(6-(5-Isopropyl-2-methoxyphenyl)-3-nitropyridin-2-ylamino)-3-methylbutan-1-ol. To a solution of (S)-2-(6-Chloro-3-nitropyridin-2-ylamino)-3-methylbutan-1-ol (0.80 g, 3.08 mmol) and 5-isopropyl-2-methoxyphenylboronic acid (0.78 g, 4.00 mmol) in DMF (50 mL) was added potassium carbonate (1.7 g, 12.3 mmol) in water (8 mL). The reaction solution was purged with a stream of nitrogen followed by the addition of tetrakis(triphenylphosphine) palladium(0) (0.358 g, 0.308 mmol). After heating at 85° C. for 2 h, the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography to afford the title compound (1.11 g, 96% yield). MS (ESI) m/z 374.3 [M+1]+.

Workup

customThe reaction solution was purged with a stream of nitrogen
customthe solvent was removed under reduced pressure
customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-200cc98a2d3242b597030779cdd64050
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372976B2

Reaction notes

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