Toluene → HCID 66604864, compound

HRID 2410702Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])=[CH:13][CH:12]=2)=[C:6]([CH:9]=1)[C:7]#[N:8].C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1.[CH3:38][C:39]1[CH:40]=[C:41](B(O)O)[CH:42]=[CH:43][C:44]=1[CH3:45]>CO.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:38][C:39]1[CH:40]=[C:41]([C:2]2[CH:3]=[CH:4][C:5]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[O:18])=[CH:13][CH:12]=3)=[C:6]([C:7]#[N:8])[CH:9]=2)[CH:42]=[CH:43][C:44]=1[CH3:45]

Participants

Conditions

Temperature: 105 °C

Procedure

5-Bromo-2-(4-(morpholine-4-carbonyl)phenylamino)benzonitrile (300 mg, 0.777 mmol), Pd(Ph3P)4 (44.9 mg, 0.039 mmol), aqueous 2M Na2CO3 (0.882 mL, 1.763 mmol) were mixed with toluene (4 mL) in a sealed microwave tube. 3,4-dimethylphenylboronic acid (163 mg, 1.087 mmol) in MeOH (2.00 mL) was added to the above mixture. The mixture was heated at 105° C. for 4 hrs in an oil bath. The crude was diluted with CH2Cl2 (100 ml) and washed with water (2×50 ml), brine, dried with MgSO4 and concentrated. 378 mg of crude product (77% purity) was obtained and it will be used as it is.

Workup

washwashed with water (2×50 ml), brine
dry with materialdried with MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-64b21d5e65644a2fbe445bfc8ecfa5d5
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

Loading…