2-Methoxyethanol → HCID 67347508, compound

HRID 1676367Notes

Reaction equation

HRID 1676367 reaction equation
C[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+].COCCO>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.[OH-].[Na+]>[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]([OH:2])=[O:4])=[CH:6][CH:7]=4)[S:31][C:24]=23)=[C:15]([F:14])[CH:16]=1

Participants

7

Reactant 4

HCID 80192-MethoxyethanolHCID 10796Cesium carbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

Product 1

HCID 67347508HCID 67347508, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A round-bottomed flask was charged with 4-(methoxycarbonyl)phenylboronic acid (4.95 g, 27.5 mmol), 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)aniline (Example 6, Step A, 7.08 g, 18.3 mmol), cesium carbonate (8.96 g, 27.5 mmol) and 2-methoxyethanol (1.40 g, 18.3 mmol) (100 mL). The mixture was purged with nitrogen for 10 minutes and then Pd(PPh3)4 (1.27 g, 1.10 mmol) was added as a solid. The mixture was heated under nitrogen to 90° C. for 48 hours and then cooled to room temperature. NaOH (10 mL, 5N) was added and the mixture was stirred for 2 hours. The mixture was extracted with EtOAc (2×300 mL). The aqueous phase was acidified with HCl (2N) to pH 7. The formed precipitate was collected by filtration and washed with water to get the product (7.6 g, 109%, contains residual water) as a beige solid. LRMS (esi+) 381 m/z (M+1) detected.

Workup

  1. customThe mixture was purged with nitrogen for 10 minutes
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with EtOAc (2×300 mL)
  4. filtrationThe formed precipitate was collected by filtration
  5. washwashed with water
  6. customto get the product (7.6 g, 109%, contains residual water) as a beige solid

Sources & evidence

ORD record
ord-9c4d26fe50bc49ce9b124791191031f6
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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