5-Azaindole → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879465

Reaktionsgleichung

Reaktionsgleichung von HRID 879465
[C:1]([O:5][C@@H:6]([C:10]1[C:34]([CH3:35])=[CH:33][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21]N=C(N4CC5C=CN=CC=5C4=O)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[C:44]1SC2C(C3C=CC(Cl)=CC=3)=C([C@H](OC(C)(C)C)C(OCC)=O)[C:50]([CH3:71])=[CH:49][C:47]=2[N:48]=1.N1C2C=CN=CC=2C=C1.C1C2C=CN=CC=2C(=[O:90])N1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]([O:5][C@@H:6]([C:10]1[C:34]([CH3:35])=[CH:33][C:13]2[N:14]=[C:15]([C:17]3[CH:18]=[C:49]4[C:47](=[CH:21][CH:22]=3)[N:48]([CH3:44])[C:71](=[O:90])[CH2:50]4)[S:16][C:12]=2[C:11]=1[C:36]1[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 92205-AzaindoleHCID 205051661,2-Dihydro-3H-pyrrolo(3,4-c)pyridin-3-oneHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetateHCID 86700276(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(3-oxo-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

Produkt 1

HCID 86700274(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418851HCID 178418851, VerbindungKatalysator

Versuchsvorschrift

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-2-oxoindolin-5-yl)benzo[d]thiazol-6-yl)acetic acid was prepared in a similar manner as (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(3-oxo-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid except (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate was used instead of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate, 1H-pyrrolo[3,2-c]pyridine was used instead 1H-pyrrolo[3,4-c]pyridin-3(2H)-one and Pd(P-tBu3)2 was used instead of Pd2(dba)3 LCMS-ESI+: calc'd C27H25ClN3O3S: 506.0 (M+H+); Found: 506.2 (M+H+). 1H NMR (400 MHz, CD3OD) δ: 9.31 (s, 1H), 9.18 (d, 1H), 8.66 (d, 1H), 8.31 (d, 1H), 7.90 (s, 1H), 7.72-7.70 (m, 1H), 7.63-7.61 (m, 3H), 7.32 (d, 1H), 5.26 (s, 1H), 2.63 (s, 3H), 0.98 (s, 9H).

Quellen und Nachweise

ORD-Eintrag
ord-f0964f561cd441e09d5a914efedae227
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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