Sodium Carbonate → HCID 46238783, compound

HRID 2066561Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[CH2:10][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([CH:20]4[CH2:22][CH2:21]4)[CH2:16][CH2:15]3)(C=O)[S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:37]2[CH:45]=[C:44]([C:46]#[N:47])[CH:43]=[C:42]3[C:38]=2[CH:39]=[CH:40][NH:41]3)O1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(#N)C.ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:20]1([N:17]2[CH2:16][CH2:15][N:14]([CH2:13][C:9]3[S:8][C:6]4[N:7]=[C:2]([C:37]5[CH:45]=[C:44]([C:46]#[N:47])[CH:43]=[C:42]6[C:38]=5[CH:39]=[CH:40][NH:41]6)[N:3]=[C:4]([N:23]5[CH2:24][CH2:25][O:26][CH2:27][CH2:28]5)[C:5]=4[CH:10]=3)[CH2:19][CH2:18]2)[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-chloro-6-(4-cyclopropyl-piperazin-1ylmethyl)-4-morpholin-4-yl-thieno[2,3-d]pyrimidine-6-carbaldehyde (217 mg), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-H-indole-6-carbonitrile (256 mg), bis(triphenylphosphine)palladium chloride (19 mg), and sodium carbonate (175 mg) in water (1.7 mL) and acetonitrile (6 mL) was heated in a microwave reactor at 140° C. for 1 hour. The reaction mixture was cooled, diluted with dichloromethane (20 mL), washed with water, dried (MgSO4) and the solvents removed in vacuo to give, after purification using flash chromatography, the title compound (59 mg) as a white solid.

Workup

temperatureThe reaction mixture was cooled
washwashed with water
dry with materialdried (MgSO4)
customthe solvents removed in vacuo
customto give
customafter purification

Sources & evidence

ORD record: ord-d818ee0b33354a9cb7df816d928d3d3b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293735B2

Reaction notes

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