Methyl 4-(bromomethyl)-3-methoxybenzoate → 4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid

HRID 1080754Notes

Reaction equation

HRID 1080754 reaction equation
BrC1C2C(=CC=C(NC(OC3CCCC3)=O)C=2)N(C)N=1.BrCC1C=CC(C(OC)=O)=CC=1OC.[CH:35]1([O:40][C:41]([NH:43][C:44]2[CH:45]=[C:46]3[C:50](=[CH:51][CH:52]=2)[N:49]([CH3:53])[N:48]=[C:47]3[CH2:54][C:55]2[CH:64]=[CH:63][C:58]([C:59]([O:61]C)=[O:60])=[CH:57][C:56]=2[O:65][CH3:66])=[O:42])[CH2:39][CH2:38][CH2:37][CH2:36]1>[Zn].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]>[CH:35]1([O:40][C:41]([NH:43][C:44]2[CH:45]=[C:46]3[C:50](=[CH:51][CH:52]=2)[N:49]([CH3:53])[N:48]=[C:47]3[CH2:54][C:55]2[CH:64]=[CH:63][C:58]([C:59]([OH:61])=[O:60])=[CH:57][C:56]=2[O:65][CH3:66])=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

6

Reactant 3

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 14626827Methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoateHCID 233659043-Bromo-5-(cyclopentyloxycarbonyl)amino-1-methylindazole

Product 1

HCID 146268294-[5-(Cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×

Procedure

The process may be carried out, for example, using a stoichiometric amount of activated zinc dust and a catalytic quantity of a transition metal catalyst, such as, for example, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) or dichlorobis(triphenylphosphine)nickel (II) to couple, for example, 3-bromo-5-(cyclopentyloxycarbonyl)amino-1-methylindazole with, for example, methyl 4-bromomethyl-3-methoxybenzoate to afford methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol -3-ylmethyl]-3-methoxybenzoate; followed by decomposition of the ester to afford 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindazol-3-ylmethyl]-3-methoxybenzoic acid.

Sources & evidence

ORD record
ord-47cc39c612714b67abc80c7baf4f8030
Source dataset
uspto-grants-1996_12
Patent number
US05583152

Reaction notes

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