HCID 67393677, compound → HCID 68239396, compound

HRID 1776875Notes

Reaction equation

HRID 1776875 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]2[CH:11]([CH:28]3[CH2:30][CH2:29]3)[O:12][C:13]3[CH:18]=[CH:17][C:16](B4OC(C)(C)C(C)(C)O4)=[CH:15][C:14]=3[C:3]=12.Br[C:32]1[C:33]([N:52]([CH3:57])[S:53]([CH3:56])(=[O:55])=[O:54])=[CH:34][C:35]2[O:39][C:38]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=3)=[C:37]([C:47]([NH:49][CH3:50])=[O:48])[C:36]=2[CH:51]=1>CN(C=O)C.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:1][C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]2[CH:11]([CH:28]3[CH2:30][CH2:29]3)[O:12][C:13]3[CH:18]=[CH:17][C:16]([C:32]4[C:33]([N:52]([CH3:57])[S:53]([CH3:56])(=[O:55])=[O:54])=[CH:34][C:35]5[O:39][C:38]([C:40]6[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=6)=[C:37]([C:47]([NH:49][CH3:50])=[O:48])[C:36]=5[CH:51]=4)=[CH:15][C:14]=3[C:3]=12

Participants

5

Reactant 2

HCID 67393677HCID 67393677, compoundHCID 71295532HCID 71295532, compound

Product 1

HCID 68239396HCID 68239396, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 12-chloro-6-cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6H-benzo[5,6][1,3]oxazino[3,4-a]indole (40 mg, 0.10 mmol), 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (45 mg, 0.10 mmol), K3PO4-3H2O (80 mg, 0.30 mmol) and Pd(dppf)Cl2 (7 mg, 0.01 mmol) in 2 mL of DMF was heated in a sealed tube under microwave condition at 100° C. for 20 minutes, and then the mixture was purified using prep-HPLC to provide Compound 131 (35 mg, yield: 55.1%). 1H-NMR (CDCl3, 400 MHz) δ 8.39 (s, 1H), 7.96˜7.93 (t, J=8.0 Hz, 2H), 7.85 (s, 1H), 7.64 (d, J=6.8 Hz, 2H), 7.40 (d, J=4.4 Hz, 2H), 7.30 (d, J=7.2 Hz, 1H), 7.23˜7.20 (m, 4H), 5.94 (s, 1H), 5.77 (d, J=7.2 Hz, 1H), 3.29 (s, 3H), 3.00 (d, J=4.8 Hz, 3H), 2.62 (s, 3H), 1.55˜1.50 (m, 1H), 0.66˜0.60 (m, 4H). MS (M+H)+: 670.

Workup

  1. customthe mixture was purified

Sources & evidence

ORD record
ord-0812b3e406414e1fa20240a3d4088565
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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