Sodium Bicarbonate → HCID 69512722, compound

HRID 1272718Notes

Reaction equation

HRID 1272718 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[O:7])=[C:4]([F:15])[CH:3]=1.[CH:16]1([NH:19][C:20](=[O:37])[C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[C:23](B3OC(C)(C)C(C)(C)O3)[CH:22]=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:16]1([NH:19][C:20]([C:21]2[CH:26]=[C:25]([C:2]3[CH:14]=[CH:13][C:5]([C:6]([NH:8][CH2:9][CH:10]4[CH2:12][CH2:11]4)=[O:7])=[C:4]([F:15])[CH:3]=3)[C:24]([CH3:27])=[CH:23][CH:22]=2)=[O:37])[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 18457805HCID 18457805, compound2×HCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 69512722HCID 69512722, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

4-Bromo-N-cyclopropylmethyl-2-fluorobenzamide (Intermediate 14, 60 mg), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (60 mg), tetrakis(triphenylphosphine)palladium (2.5 mg) and aqueous sodiumhydrogen carbonate (1M, 1 ml) were heated in propan-2-ol (2 ml) at 85° C. for 18 hours. The reaction was concentrated under vacuum and the residue applied to a SPE (Si, 2 g) and eluted with 1:3 and 3:1 ethyl acetate/cyclohexane. The solvent was evaporated from the latter fraction under vacuum and the residue triturated with ether to give N3-cyclopropyl-N4′-(cyclopropylmethyl)-3′-fluoro-6-methyl-1,1′-biphenyl-3,4′-dicarboxamide.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. washeluted with 1:3 and 3:1 ethyl acetate/cyclohexane
  3. customThe solvent was evaporated from the latter fraction under vacuum
  4. customthe residue triturated with ether

Sources & evidence

ORD record
ord-cd10eecdd8224cb2b4f1e4cb81ab4bb2
Source dataset
uspto-grants-2007_04
Patent number
US07208629B2

Reaction notes

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