Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate → 3-(3-Quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-benzoic acid

HRID 69171Notes

Reaction equation

HRID 69171 reaction equation
Cl[C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:17]([CH2:20][C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)=[CH:18][N:19]=3)[N:16]=2)[CH:8]=[CH:7][C:3]=1C(N)=O.C([O:33][C:34](=[O:50])C1C=CC=C(B2OC(C)(C)C(C)(C)O2)C=1)C>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].C(Cl)Cl>[N:27]1[C:28]2[C:23](=[CH:22][C:21]([CH2:20][C:17]3[N:15]4[N:16]=[C:11]([C:9]5[CH:10]=[C:2]([CH:3]=[CH:7][CH:8]=5)[C:34]([OH:50])=[O:33])[CH:12]=[CH:13][C:14]4=[N:19][CH:18]=3)=[CH:30][CH:29]=2)[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 2773966Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 442062952-Chloro-4-(3-quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-benzamide

Product 1

HCID 442085693-(3-Quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

The title compound was prepared in analogy to the compound of Example 15 starting with 3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid ethyl ester, using PdCl2(dppf)/CH2Cl2 (1/1) as catalyst and with an additional ester deprotection step afterwards (tR 3.14 min (conditions 11), MH+=380.9).

Sources & evidence

ORD record
ord-d428857b4c9b44e5aeee1e6746feebd7
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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