Sodium Carbonate → 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester

HRID 1892620Notes

Reaction equation

HRID 1892620 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]1[CH:30]=[CH:29][C:14]([CH2:15][CH:16]2[C:25]3[CH:24]=[C:23]4[O:26][CH2:27][O:28][C:22]4=[CH:21][C:20]=3[CH2:19][CH2:18][NH:17]2)=[CH:13][CH:12]=1.[C:31]([O:35][C:36](N1CCC2C=C3OCOC3=CC=2C1CC1C=CC(Br)=CC=1)=[O:37])([CH3:34])([CH3:33])[CH3:32].COC1C=CN=CC=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CC(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:31]([O:35][C:36]([N:17]1[CH2:18][CH2:19][C:20]2[CH:21]=[C:22]3[O:28][CH2:27][O:26][C:23]3=[CH:24][C:25]=2[CH:16]1[CH2:15][C:14]1[CH:13]=[CH:12][C:11]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[O:4][CH3:3])=[CH:30][CH:29]=1)=[O:37])([CH3:34])([CH3:33])[CH3:32]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27625564-Methoxypyridine-3-boronic acidHCID 597442655-(4-Bromobenzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl esterHCID 690813235-[4-(4-Methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline dihydrochloride salt

Product 1

HCID 597442885-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3776IsopropanolSolvent

Procedure

The synthesis of 5-[4-(4-methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline dihydrochloride salt 45 is shown in Scheme-12. Reaction of compound 38 with 4-methoxypyridine-3-boronic acid 19 in the presence of Palladium (II) acetate, triphenylphosphine, and Na2CO3 in anhydrous 2-propanol yielded 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 43 which was treated with trifluoroacetic acid in dichloromethane to get 5-[4-(4-methoxypyridin-3-yl)benzyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline trifluoro acetate salt 44. Compound 44 was treated by 37% HCl, 1N NaOH followed by 2M HCl/Ether in MeOH-Ether to obtain 45.

Sources & evidence

ORD record
ord-efa10c3d971f4af58a9df489c86e31ce
Source dataset
uspto-grants-2013_08
Patent number
US08507523B2

Reaction notes

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