Cesium carbonate → HCID 117652846, compound

HRID 588393Notes

Reaction equation

[CH3:1][N:2]1[C:6]2=[C:7]([N:11]([C@@H:29]3[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]3)[C:12](=[O:28])[C:13]3[CH:18]=[CH:17][C:16](B4OC(C)(C)C(C)(C)O4)=[CH:15][CH:14]=3)[N:8]=[CH:9][CH:10]=[C:5]2[CH:4]=[CH:3]1.Br[C:43]1[CH:44]=[N:45][N:46]([CH3:53])[C:47]=1[C:48]([O:50][CH2:51][CH3:52])=[O:49].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:51]([O:50][C:48]([C:47]1[N:46]([CH3:53])[N:45]=[CH:44][C:43]=1[C:16]1[CH:17]=[CH:18][C:13]([C:12]([N:11]([C@@H:29]2[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[CH2:30]2)[C:7]2[N:8]=[CH:9][CH:10]=[C:5]3[CH:4]=[CH:3][N:2]([CH3:1])[C:6]=23)=[O:28])=[CH:14][CH:15]=1)=[O:49])[CH3:52]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of the compound from Step 1 (R)-tert-butyl 3-(N-(1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)piperidine-1-carboxylate (0.5 g, 0.89 mmol) in 1,4-dioxane (10 mL) was added ethyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylate (0.21 g, 0.90 mmol), Pd(dppf)Cl2 (0.065 g, 0.089 mmol) and Cs2CO3 (0.58 g, 1.78 mmol). The reaction was heated 85° C. for 16 h. The reaction mixture was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography eluting with a gradient of petroleum ether: EtOAc (5:1 to 0:1) to afford the title compound (0.45 g, 86%) as yellow solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe resulting crude product was purified by silica gel chromatography
washeluting with a gradient of petroleum ether: EtOAc (5:1 to 0:1)

Sources & evidence

ORD record: ord-5f06f26f23a84c3796febd79371712a2
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227956B2

Reaction notes

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