Cesium carbonate → HCID 57637381, compound

HRID 2078714Notes

Reaction equation

[CH2:1]([O:8][CH2:9][N:10]1[C:14]2[CH:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[C:29]([C:31]1[S:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[C:32]=1Br)=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:41](=[N:54][NH2:55])([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.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.[Fe+2]>[C:41](=[N:54][NH:55][C:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[S:35][C:31]=1[C:29]([C:11]1[N:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]2[CH:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:17]=[CH:18][C:13]=2[N:12]=1)=[O:30])([C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of [1-benzyloxymethyl-6-(3-piperidin-1-yl-propoxy)-1H-benzoimidazol-2-yl]-(3-bromo-benzo[b]thiophen-2-yl)-methanone [40 mg, Intermediate (42)], benzophenone hydrazone (18 mg, 1.4 eq), Pd(OAc) (0.9 mg, 0.05 eq)), DPPF (3.8 mg, 0.1 eq) and cesium carbonate (33.7 mg, 1.6 eq) in 5 ml toluene under nitrogen was heated at 90° C. overnight. The reaction was cooled to room temperature and the mixture was passed through a SCX column and eluted with 7N ammonia in methanol to yield [3-(N′-benzhydrylidene-hydrazino)-benzo[b]thiophen-2-yl]-[1-benzyloxymethyl-6-(3-piperidin-1-yl-propoxy)-1H-benzoimidazol-2-yl]-methanone [200 mg, Intermediate (43)].

Workup

temperatureThe reaction was cooled to room temperature
washeluted with 7N ammonia in methanol

Sources & evidence

ORD record: ord-969d8e40777443028c4107382f3b2a7f
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928231B2

Reaction notes

Loading…