Potassium Carbonate → HCID 59793201, compound

HRID 1968379Notes

Reaction equation

[C:1]1([N:7]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27](B4OC(C)(C)C(C)(C)O4)=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:39][C:40]1[CH:45]=[CH:44][C:43](I)=[CH:42][CH:41]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[Br:39][C:40]1[CH:45]=[CH:44][C:43]([C:27]2[CH:26]=[CH:25][C:24]([C:21]3[CH:20]=[CH:19][C:18]([N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:8]4[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[CH:11]=[CH:10][CH:9]=4)=[CH:23][CH:22]=3)=[CH:29][CH:28]=2)=[CH:42][CH:41]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of Compound 5 (4.5 g, 9.0 mmol), 1-bromo-4-iodobenzene (5.12 g, 18 mmol), Pd(PPh3)4 (0.52 g, 0.45 mmol) and potassium carbonate (4.436 g, 32 mmol) in dioxane/water (150 ml/30 ml) was degassed and heated at 95° C. overnight. After being cooled to RT, the mixture was poured into dichloromethane (300 ml), washed with brine, dried over Na2SO4, then loaded on silica gel, purified by flash column (hexanes to hexanes/ethyl acetate 20:1) to give a light yellow solid (4.30 g, in 90.7% yield).

Workup

customwas degassed
temperatureAfter being cooled to RT
additionthe mixture was poured into dichloromethane (300 ml)
washwashed with brine
dry with materialdried over Na2SO4
custompurified by flash column (hexanes to hexanes/ethyl acetate 20:1)
customto give a light yellow solid (4.30 g, in 90.7% yield)

Sources & evidence

ORD record: ord-d1d21ac2739640f9b48e5e82ce6a51fd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426040B2

Reaction notes

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