2-Methoxyethanol → HCID 67347334, compound

HRID 1676327Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].[F:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[O:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]2[CH:29]=[C:30](I)[S:31][C:24]=12)[NH2:18].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:39][O:40][CH2:41]CO>O.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>[NH2:18][C:17]1[CH:19]=[CH:20][C:21]([O:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]3[CH:29]=[C:30]([C:8]4[CH:9]=[CH:10][C:5]([C:3]([O:2][CH2:1][CH2:39][O:40][CH3:41])=[O:4])=[CH:6][CH:7]=4)[S:31][C:24]=23)=[C:15]([F:14])[CH:16]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A round-bottomed flask was charged with 4-(methoxycarbonyl)phenylboronic acid (0.472 g, 2.62 mmol), 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)aniline (Example 6, Step A, 0.750 g, 1.94 mmol), cesium carbonate (0.949 g, 2.91 mmol), and 2-methoxyethanol (10 mL). The mixture was purged with nitrogen for 10 minutes and then Pd(PPh3)4 (0.135 g, 0.117 mmol) was added. The mixture was heated under nitrogen to 85° C. for 18 hours and then cooled to room temperature. The mixture was diluted with water (30 mL) and the resulting precipitate collected by filtration. After drying under high vacuum, the product was isolated (0.26 mg, 25%) as an off-white solid. LRMS (esi+) 439 m/z (M+1) detected.

Workup

customThe mixture was purged with nitrogen for 10 minutes
temperaturecooled to room temperature
filtrationthe resulting precipitate collected by filtration
customAfter drying under high vacuum
customthe product was isolated (0.26 mg, 25%) as an off-white solid

Sources & evidence

ORD record: ord-d0e1219c37554f8aaded9b68fbebc6d4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003662B2

Reaction notes

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