Sodium Bicarbonate → HCID 44479931, compound

HRID 1272725Notes

Reaction equation

Br[C:2]1[C:3]([CH3:15])=[CH:4][C:5]([F:14])=[C:6]([CH:13]=1)[C:7]([NH:9][CH:10]1[CH2:12][CH2:11]1)=[O:8].[CH:16]1([CH2:19][NH:20][C:21](=[O:37])[C:22]2[CH:27]=[CH:26][C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=2)[CH2:18][CH2:17]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>[CH:10]1([NH:9][C:7]([C:6]2[CH:13]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([C:21]([NH:20][CH2:19][CH:16]4[CH2:18][CH2:17]4)=[O:37])=[CH:23][CH:24]=3)[C:3]([CH3:15])=[CH:4][C:5]=2[F:14])=[O:8])[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromo-N-cyclopropyl-2-fluoro-4-methylbenzamide (Intermediate 22, 30 mg), N-cyclopropylmethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide (28 mg), tetrakis(triphenylphosphine)palladium (1 mg) and aqueous sodiumhydrogen carbonate (1M, 0.5 ml) were mixed in propan-2-ol (2 ml) and heated at 90° C. under nitrogen for 24 hrs. The reaction was absorbed onto silica and applied to a SPE (Si, 5 g) and eluted with an ethyl acetate/cyclohexane gradient (0–100% ethyl acetate). The product fractions were reduced to dryness under vacuum and the residue recrystallised from ethyl acetate to give N3-cyclopropyl-N4′-(cyclopropylmethyl)-4-fluoro-6-methyl-1,1′-biphenyl-3,4′-dicarboxamide.

Workup

customThe reaction was absorbed onto silica
washeluted with an ethyl acetate/cyclohexane gradient (0–100% ethyl acetate)
customthe residue recrystallised from ethyl acetate

Sources & evidence

ORD record: ord-bf76ea97c2e845a79d26be7457a1a87a
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208629B2

Reaction notes

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