Methyl 4-(bromomethyl)-3-methoxybenzoate → HCID 19822475, compound

HRID 728672Notes

Reaction equation

HRID 728672 reaction equation
BrC1C2C(=CC=C(C(=O)NCC3CCCC3)C=2)N(CC(=O)N)N=1.BrCC1C=CC(C(OC)=O)=CC=1OC.[CH:38]1([CH2:43][NH:44][C:45]([C:47]2[CH:48]=[C:49]3[C:53](=[CH:54][CH:55]=2)[N:52]([CH2:56][C:57](=[O:59])[NH2:58])[N:51]=[C:50]3[CH2:60][C:61]2[CH:70]=[CH:69][C:64]([C:65]([O:67]C)=[O:66])=[CH:63][C:62]=2[O:71][CH3:72])=[O:46])[CH2:42][CH2:41][CH2:40][CH2:39]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].Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:38]1([CH2:43][NH:44][C:45]([C:47]2[CH:48]=[C:49]3[C:53](=[CH:54][CH:55]=2)[N:52]([CH2:56][C:57](=[O:59])[NH2:58])[N:51]=[C:50]3[CH2:60][C:61]2[CH:70]=[CH:69][C:64]([C:65]([OH:67])=[O:66])=[CH:63][C:62]=2[O:71][CH3:72])=[O:46])[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

7

Reactant 3

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 19822474HCID 19822474, compoundHCID 19822476HCID 19822476, compound

Product 1

HCID 19822475HCID 19822475, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178418751HCID 178418751, compoundCatalyst

Procedure

The cross coupling 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-(N-cyclopentylmethylcarbamoyl)-1-(carbamoylmethyl)indazole with, for example, methyl 4-bromomethyl-3-methoxybenzoate to afford methyl 4-[5-(N-cyclopentylmethylcarbamoyl)-1-(carbamoylmethyl)indazol-3-ylmethyl]-3-methoxybenzoate; followed by decomposition of the ester to afford 4-[5-(N-cyclopentylmethylcarbamoyl)-1-(carbamoylmethyl)indazol-3-ylmethyl]-3-methoxybenzoic acid.

Sources & evidence

ORD record
ord-60e63219973a4bb981904b333322d874
Source dataset
uspto-grants-1991_09
Patent number
US05049679

Reaction notes

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