Water → HCID 68328233, compound

HRID 634330Notes

Reaction equation

HRID 634330 reaction equation
[CH:1]([NH:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=[C:13]3B2OC(C)(C)C(C)(C)O2)=[N:8][N:9]=1)([CH3:3])[CH3:2].Br[C:39]1[CH:47]=[CH:46][C:42]([C:43]([OH:45])=[O:44])=[CH:41][C:40]=1[F:48].O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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:48][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][C:39]=1[C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([C:7]3[O:6][C:5]([NH:4][CH:1]([CH3:2])[CH3:3])=[N:9][N:8]=3)[CH:11]=2)[N:15]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=1)[C:43]([OH:45])=[O:44]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27733414-Bromo-3-fluorobenzoic acidHCID 68328163HCID 68328163, compound

Product 1

HCID 68328233HCID 68328233, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-isopropyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (2.0 g, 3.831 mmol) and 4-bromo-3-fluorobenzoic acid (1.2 g, 5.74 mmol, Sigma-Aldrich) in DME (38 mL)/water (9 mL) was added Na2CO3 (1.35 g, 11.5 mmol) and Pd(PPh3)4 (439 mg, 0.38 mmol) and Ar gas was bubbled for 5 min. The reaction mixture was heated at 90° C. for 4 h. The reaction was quenched with water (200 mL) to get a brown precipitate. The precipitate was filtered, washed with water (2×100 mL) and dried to give crude product (1.0 g), which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 535.1 (M+1).

Workup

  1. customwas bubbled for 5 min
  2. customThe reaction was quenched with water (200 mL)
  3. customto get a brown precipitate
  4. filtrationThe precipitate was filtered
  5. washwashed with water (2×100 mL)
  6. customdried

Sources & evidence

ORD record
ord-6c2092c8ec83496b843cebe9cab68825
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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