Water → HCID 68328685, compound

HRID 634315Notes

Reaction equation

HRID 634315 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[N:44]=[C:43]([C:45]([OH:47])=[O:46])[CH:42]=[CH:41][CH:40]=1.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>[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:20])=[O:21])[CH:14]=[C:13]3[C:39]2[N:44]=[C:43]([C:45]([OH:47])=[O:46])[CH:42]=[CH:41][CH:40]=2)=[N:8][N:9]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5939196-Bromopyridine-2-carboxylic acidHCID 68328163HCID 68328163, compound

Product 1

HCID 68328685HCID 68328685, compound

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 (500 mg, 0.957 mmol) and 6-bromopicolinic acid (280 mg, 1.436 mmol, Sigma-Aldrich) in DME (10 mL)/water (2.5 mL) was added Na2CO3 (304 mg, 2.871 mmol) and Pd(PPh3)4 (111 mg, 0.096 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, which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 518.2 (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
  7. customto give crude product, which
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-bfaf32a64433484ea78fa069e8398866
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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