Sodium Carbonate → HCID 21865353, compound

HRID 859034Notes

Reaction equation

HRID 859034 reaction equation
Br[C:2]1[C:3]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[CH:4][C:5]([O:8][C:9]2[C:14]3[N:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[S:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[F:32][C:33]([F:45])([F:44])[O:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1.[C:46]([O-])([O-:48])=[O:47].[Na+].[Na+]>O1CCOCC1.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>[F:45][C:33]([F:32])([F:44])[C:46]([OH:48])=[O:47].[F:32][C:33]([F:44])([F:45])[O:34][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[C:3]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[CH:4][C:5]([O:8][C:9]3[C:14]4[N:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[S:17][C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:6][CH:7]=2)=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 21865157HCID 21865157, compound

Product 1

HCID 21865353HCID 21865353, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

This material was prepared analogous to Example 146 by using N-{4-[5-bromo-4-(4-trifluoromethyl-phenyl)-pyridin-2-yloxy]-benzothiazol-2-yl}-acetamide, (Example 145(b)), (0.1 g, 0.2 mmol), 4-(trifluoromethoxy)phenyl boronic acid (53 mg, 0.26 mmol, Aldrich), Pd(PPh3)4 (23 mg, 0.02 mmol, Aldrich) and aq. Na2CO3 (32 mg in 0.4 mL of water) in dioxane (2 mL). Purification by silica gel chromatography (1:2 of EtOAc/hexanes), followed by preparative HPLC separation gave the title compound as a white solid. MS (ESI, pos. ion) m/z: 590 (M+1). Mp: 212.9–222.3° C.

Workup

  1. customThis material was prepared analogous to Example 146
  2. customPurification by silica gel chromatography (1:2 of EtOAc/hexanes)
  3. customfollowed by preparative HPLC separation

Sources & evidence

ORD record
ord-c5e8d34ccc244f2b95c4860c972014aa
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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