Sodium Carbonate → HCID 117642124, compound

HRID 922768Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH:17]=[C:16]([C@@:18]([OH:25])([CH2:23][CH3:24])[C:19]([F:22])([F:21])[F:20])[N:15]=[N:14]3)=[CH:9][CH:10]=2)[N:5]=[C:4]([C:26]([NH2:28])=[O:27])[CH:3]=1.[CH3:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[OH:25][C@@:18]([C:16]1[N:15]=[N:14][N:13]([CH2:12][C:8]2[CH:7]=[C:6]3[C:11]([C:2]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[CH3:29])=[CH:3][C:4]([C:26]([NH2:28])=[O:27])=[N:5]3)=[CH:10][CH:9]=2)[CH:17]=1)([C:19]([F:22])([F:21])[F:20])[CH2:23][CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

4-chloro-7-({4-[(2S)-1,1,1-trifluoro-2-hydroxybutan-2-yl]-1H-1,2,3-triazol-1-yl}methyl)quinoline-2-carboxamide (3-14, 8 mg, 0.02 mmol, 1.0 equiv.), (2-methylphenyl)boronic acid (5 mg, 0.04 mmol, 2 equiv.), Pd(PPh3)4 (0.7 mg, 0.0006 mmol, 0.03 equiv.) and 2M aqueous Na2CO3 (0.02 mL, 0.05 mmol, 2.5 equiv.) were suspended in Dioxane (0.4 mL) and the reaction mixture was heated overnight at 100° C. The crude mixture was filtered, concentrated and purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier) to afford 7-({4-[(1S)-1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)-4-(2-methylphenyl)quinoline-2-carboxamide (3-15). LRMS m/z (M+H)+ 470.1 found, 470.2 required.

Workup

filtrationThe crude mixture was filtered
concentrationconcentrated
custompurified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier)

Sources & evidence

ORD record: ord-b76bf372d7e349f1a87b2a9756dced88
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278960B2

Reaction notes

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