Dichloromethane → HCID 86696350, compound

HRID 870653Notes

Reaction equation

HRID 870653 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19](Br)=[CH:20][N:21]=2)[N:18]=1)[CH3:12])([CH3:4])([CH3:3])[CH3:2].[C:24]([C:27]1[S:31][C:30](B(O)O)=[CH:29][CH:28]=1)(=[O:26])[CH3:25].O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].ClCCl>COCCOC.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].O>[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C:30]3[S:31][C:27]([C:24](=[O:26])[CH3:25])=[CH:28][CH:29]=3)=[CH:20][N:21]=2)[N:18]=1)[CH3:12])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 4143377(5-Acetylthiophen-2-yl)boronic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 86696348HCID 86696348, compound

Product 1

HCID 86696350HCID 86696350, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

(3-{[3-(5-Acetyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-methyl-amino}-propyl)-carbamic acid tert-butyl ester was prepared and isolated similarly to the procedure detailed in example 5.6.17 from a mixture of {3-[(3-bromo-imidazo[1,2-b]pyridazin-6-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester (0.5 g, 1.3 mmol), 5-acetyl-2-thiopheneboronic acid [206551-43-1] (0.3 g, 1.5 mmol), potassium phosphate tribasic monohydrate [27176-10-9] (0.5 g, 2.5 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane [95464-05-4] (0.1 g, 0.1 mmol) in a solution of 30% (v/v) water in 1,2-dimethoxyethane (30 mL) to afford 0.16 g of yellow powder, mp. 148-149° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37 (s, 9H) 1.78 (quin, J=6.95 Hz, 2H) 2.54 (s, 3H) 3.05 (q, J=6.57 Hz, 2H) 3.17 (s, 3H) 3.61 (t, J=7.20 Hz, 2H) 6.88 (br. s., 1H) 7.12 (d, J=9.85 Hz, 1H) 7.82 (d, J=4.29 Hz, 1H) 7.92 (d, J=9.85 Hz, 1H) 7.97 (d, J=4.04 Hz, 1H) 8.20 (s, 1H). LRMS (ESI) m/z 430.1 [(M+H)]+, calc'd for C21H27BN5O3S: 429.55.

Workup

  1. customisolated similarly to the procedure

Sources & evidence

ORD record
ord-2ac7b1799f054e26b2cca9bfe7dd8582
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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