Sodium Carbonate → HCID 59463569, compound

HRID 1713098Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:29]1[N:30]=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O.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:1]([O:5][C:6](=[O:27])[CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:29]3[N:30]=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=3)[CH:14]=2)[CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of [6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester (1.12 g, 3 mmol), 3-chloro-6-methyl-pyridazine (501 mg, 3.9 mmol, 1.3 eq.), Pd(PPh3)4 (104 mg, 0.009 mmol, 0.03 eq.) under nitrogen, are added dioxane (30.0 ml) and sodium carbonate aqueous solution (2.0N, 3.0 ml). The resulting mixture is stirred at 90° C. for 16 hr. The reaction mixture is diluted with EtOAc (80 ml), washed with water and brine, dried over sodium sulfate, and concentrated. The crude product is purified by silica gel flash chromatography (hexane/EtOAc 1:1) to give the title compound. MS (+VE) m/z 340.20 (M++1).

Workup

washwashed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe crude product is purified by silica gel flash chromatography (hexane/EtOAc 1:1)

Sources & evidence

ORD record: ord-25ac456cefc84c2a8e64b54d282690c4
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795262B2

Reaction notes

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