Potassium Phosphate, Tribasic → HCID 86709315, compound

HRID 529394Notes

Reaction equation

HRID 529394 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:15]3([CH2:16][O:17][CH2:18][CH2:19][C:20]([NH2:22])=[N:21]3)[C:14]3[CH:13]=[C:12]([Cl:23])[N:11]=[CH:10][C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[F:24][C:25]1[C:30](B(O)O)=[CH:29][CH:28]=[CH:27][N:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>>[Cl:23][C:12]1[N:11]=[CH:10][C:9]2[O:8][C:5]3[C:4]([C:15]4([CH2:16][O:17][CH2:18][CH2:19][C:20]([NH2:22])=[N:21]4)[C:14]=2[CH:13]=1)=[CH:3][C:2]([C:30]1[C:25]([F:24])=[N:26][CH:27]=[CH:28][CH:29]=1)=[CH:7][CH:6]=3

Participants

4

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27832702-Fluoropyridine-3-boronic acidHCID 72670105HCID 72670105, compound

Product 1

HCID 86709315HCID 86709315, compound

Conditions

Temperature
90 °C

Procedure

A vial was charged with (E)-7-bromo-3-chloro-6′,7′-dihydro-2′H-spiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazepin]-5′-amine (280.9 mg, 0.712 mmol), 2-fluoropyridin-3-ylboronic acid (150 mg, 1.068 mmol), Pd(AmPhos)2Cl2 (25.2 mg, 0.036 mmol), and potassium phosphate (453 mg, 2.135 mmol). The vial was flushed with Ar (g), then 1,4-dioxane (2669 μL) and water (890 μL) were added in sequence. The vial was sealed and heated in a microwave reactor for 20 min at 90° C. The mixture was extracted with EtOAc (3×), and the combined organic extracts were concentrated. The crude product was purified by chromatography on silica gel (0-10% MeOH/DCM) to give (E)-3-chloro-7-(2-fluoropyridin-3-yl)-6′,7′-dihydro-2′H-spiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazepin]-5′-amine as a white solid.

Workup

  1. customThe vial was flushed with Ar (g)
  2. addition1,4-dioxane (2669 μL) and water (890 μL) were added in sequence
  3. customThe vial was sealed
  4. extractionThe mixture was extracted with EtOAc (3×)
  5. concentrationthe combined organic extracts were concentrated
  6. customThe crude product was purified by chromatography on silica gel (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-5cebc6bcaf7c4920a5166764bacbca4f
Source dataset
uspto-grants-2016_05
Patent number
US09346827B2

Reaction notes

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