Dichloromethane → HCID 131724733, compound

HRID 23300Notes

Reaction equation

HRID 23300 reaction equation
Br[C:2]1[C:3]([O:12][CH2:13][CH3:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[NH2:15][C:16]1[CH:17]=[C:18]2[C:22]3=[C:23]([CH2:25][O:26][CH2:27][CH2:28][N:21]3[C@H:20]3[CH2:29][CH2:30][N:31](C(OC(C)(C)C)=O)[CH2:32][C@@H:19]23)[CH:24]=1.[Cl:40]CCl>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].[Pd]>[ClH:40].[ClH:40].[CH2:13]([O:12][C:3]1[C:2]([NH:15][C:16]2[CH:17]=[C:18]3[C:22]4=[C:23]([CH2:25][O:26][CH2:27][CH2:28][N:21]4[C@H:20]4[CH2:29][CH2:30][NH:31][CH2:32][C@@H:19]34)[CH:24]=2)=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=1)[CH3:14]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 225912723-Bromo-2-ethoxy-5-(trifluoromethyl)pyridineHCID 86586438Tert-butyl (7br,11as)-6-amino-1,2,7b,10,11,11a-hexahydro-4h-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8h)carboxylate

Product 1

HCID 131724733HCID 131724733, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Following the procedures described in Example 175 and using 3-bromo-2-ethoxy-5-(trifluoromethyl)pyridine and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane, as the palladium source, tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate from Example 56, Part B was converted into the title compound of Example 199 as a solid. ESI MS m/z 435.3 [C22H25F3N4O2+H]+.

Sources & evidence

ORD record
ord-051a955a363444adb54030d4975b5f6d
Source dataset
uspto-grants-2005_02
Patent number
US06849619B2

Reaction notes

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