Sodium Bicarbonate → HCID 10301643, compound

HRID 1272714Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:5]([NH:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:11]=[C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:9]=1)=[O:6].[CH:28]1([CH2:31][NH:32][C:33](=[O:49])[C:34]2[CH:39]=[CH:38][C:37](B3OC(C)(C)C(C)(C)O3)=[CH:36][CH:35]=2)[CH2:30][CH2:29]1.C(=O)([O-])O.[Na+]>CC(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([C:10]1[CH:9]=[C:8]([NH:7][C:5]([C:4]2[CH:3]=[C:2]([C:37]3[CH:38]=[CH:39][C:34]([C:33]([NH:32][CH2:31][CH:28]4[CH2:30][CH2:29]4)=[O:49])=[CH:35][CH:36]=3)[C:26]([CH3:27])=[CH:25][CH:24]=2)=[O:6])[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[N:11]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 85 °C

Procedure

3-Bromo-N-[3-t-butyl-1-(4-methylphenyl)-pyrazol-5-yl]-4-methylbenzamide (Intermediate 2 2, 43 mg), N-cyclopropylmethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide (33 mg), tetrakis(triphenylphosphine)palladium (2 mg) and aqueous sodiumhydrogen carbonate (1M, 0;5 ml) were mixed in propan-2-ol (2 ml) and heated at 85° C. under nitrogen for 96 hrs. The cooled reaction was absorbed onto silica and applied to a SPE cartridge (Si, 5 g) and eluted with an ethyl acetate/cylohexane gradient (0–100% ethyl acetate). The product fractions were reduced to dryness under vacuum to give N3-[3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-N4′-(cyclopropylmethyl)-6-methyl-1,1′-biphenyl-3,4′-dicarboxamide.

Workup

customThe cooled reaction
customwas absorbed onto silica
washeluted with an ethyl acetate/cylohexane gradient (0–100% ethyl acetate)

Sources & evidence

ORD record: ord-20fb620360b249b58085c8d7819b7bb6
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208629B2

Reaction notes

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