Sodium Carbonate → HCID 86702529, compound

HRID 877051Notes

Reaction equation

Cl[C:2]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]3)=[C:4]2[N:3]=1.[C:22]([O:26][C:27](=[O:48])[NH:28][C:29]1([C:33]2[CH:38]=[CH:37][C:36](B3OC(C)(C)C(C)(C)O3)=[CH:35][CH:34]=2)[CH2:32][CH2:31][CH2:30]1)([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:22]([O:26][C:27](=[O:48])[NH:28][C:29]1([C:33]2[CH:34]=[CH:35][C:36]([C:2]3[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:14][N:5]4[N:6]=[C:7]5[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]5)=[C:4]4[N:3]=3)=[CH:37][CH:38]=2)[CH2:30][CH2:31][CH2:32]1)([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

To 620 mg (2.1 mmol) 2-Chloro-9-fluoro-3-phenylpyrimido[1,2-b]indazole (intermediate example Int-1-0) and 1.1 g (2.9 mmol) {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutyl}carbamic acid tert-butyl ester in 7.2 mL 1,2 dimethoxyethane were added 3.8 mL aqueous sodium carbonate (10%) and 170 mg (0.2 mmol) 1,1 bis(diphenylphosphino)ferrocenedichloropalladium(II). The reaction mixture was stirred for 30′ in the microwave at 100° C. and subsequently evaporated to dryness. The residue (770 mg=72.7%) was used without further purification in the next step.

Workup

customsubsequently evaporated to dryness
customThe residue (770 mg=72.7%) was used without further purification in the next step

Sources & evidence

ORD record: ord-1bbea25c02064f88a1244679e68b78fe
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987286B2

Reaction notes

Loading…