Water → HCID 67416694, compound

HRID 1803504Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([O:22][CH3:23])=[N:17][N:16]=[C:15]3I)=[O:11])[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].O.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36](B(O)O)[CH:35]=1>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.CO.C1(C)C=CC=CC=1>[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([O:22][CH3:23])=[N:17][N:16]=[C:15]3[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 4-iodo-1-methoxy-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (0.128 g, 0.27 mmol), K2CO3 (0.075 g, 0.54 mmol), water (0.5 mL), toluene (3 mL), methanol (3 mL), 3-pyridineboronic acid (0.04 g, 0.325 mmol), Pd(PPh3)4 (0.094 g, 0.081 mmol) was heated to 65° C. for 2 hour. The reaction was cooled, filtered through celite, rinsed with methanol and concentrated. The residue was taken up in EtOAc, washed with sat. aq. NaHCO3 and dried (Na2SO4). Column chromatography (Hex/EtOAc) afforded 1-methoxy-4-pyridin-2-yl-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (57 mg), m/z 425.01

Workup

temperatureThe reaction was cooled
filtrationfiltered through celite
washrinsed with methanol
concentrationconcentrated
washwashed with sat. aq. NaHCO3
dry with materialdried (Na2SO4)

Sources & evidence

ORD record: ord-4cc8b408b63247ec89b5d11d53cfbdaa
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349836B2

Reaction notes

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