Sodium Carbonate → HCID 42636083, compound

HRID 1971027Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9](Br)=[CH:10][C:11]3[C:12]4[C:20]([NH:21][C@H:22]([CH:27]5[CH2:29][CH2:28]5)[C:23]([F:26])([F:25])[F:24])=[N:19][CH:18]=[C:17]([C:30]([NH2:32])=[O:31])[C:13]=4[NH:14][C:15]=3[CH:16]=2)=[CH:4][N:3]=1.[CH3:34]B1OB(C)OB(C)O1.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>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9]([CH3:34])=[CH:10][C:11]3[C:12]4[C:20]([NH:21][C@H:22]([CH:27]5[CH2:29][CH2:28]5)[C:23]([F:26])([F:25])[F:24])=[N:19][CH:18]=[C:17]([C:30]([NH2:32])=[O:31])[C:13]=4[NH:14][C:15]=3[CH:16]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-(2-aminopyrimidin-5-yl)-8-bromo-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide (100 mg, 0.19 mmol), trimethylboroxin (48 mg, 0.38 mmol), Pd(PPh3)4 (11 mg, 0.0096 mmol), and sodium carbonate (61 mg, 0.58 mmol) in 1,4-dioxane (3 mL) was purged with nitrogen, heated to 100° C. overnight, and cooled to room temperature. The mixture was concentrated and purified by flash chromatography to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 11.55 (s, 1H); 8.47 (s, 1H), 8.36 (s, 1H); 8.27 (s, 2H); 7.95 (br s, 1H); 7.55 (s, 1H); 7.23 (br s, 1H); 6.91 (d, 1H); 6.73 (br s, 1H); 4.83 (m, 1H); 2.42 (s, 3H); 1.59 (m, 1H); 0.75 (m, 1H); 0.63 (m, 1H); 0.55 (m, 1H); 0.33 (m, 1H). LRMS (APCI) calc'd for (C22H20F3N7O) [M+H]+, 456.2. found 456.1.

Workup

customwas purged with nitrogen
temperaturecooled to room temperature
concentrationThe mixture was concentrated
custompurified by flash chromatography

Sources & evidence

ORD record: ord-19f2c5f48a4143ebaef56a5fe06a117a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431569B2

Reaction notes

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